Abstract A series of 2-and 3-indolylthioalkanoic acids of various chain lengths were cyclized under dehydrative conditions affording tricyclic indole-containing ring systems wherein the third ring contains a sulfur atom attached to the 2-or 3-position of the indole ring. This methodology affords entry into the novel thiepino [3, 2-b] indole, thiocino [2, 3-b] indole and thiocino [3, 2-b] indole ring systems.